Bismuth compound of aminophenols and process of making same



Patented Oct. 26, 1926. v

1 UNITED STATES PATENT OFFICE.

MAX BOCKMTTHL, OF HOCHST-ON-THE-MAIN, AND WILHELM HEINRICH LUDWIG, 0F

FRANKFORTON-THEMAIN, GERMANY, ASSIGNORS TO I. G. FARBENINDUSTRIE AKTIENGESELLSCHAFT, OF FRANKFORT, GERMANY.

BISMUTH COMPOUND 01 AMINOPHENOLS AND PROCESS OF MAKING SAME.

No Drawing". Application filed January 3, 1924, Serial No. 684,253, and in Germany January 22, 1923.

'0 have found that complex bismuth compounds of slight toxicity and having an excellent action on the spir-ochaetae and other bacteria which cause infectious diseases are obtained by acting upon amino-hydroxybenzoic acids with bismuth salts and introducing a group containing a hydroxyl, the action of the bismuth salts and the introduction of the group containing a hydroxyl being accomplished in any order of succession.

Examples.

(1) g. of the sodium salt of 3-N-di- 1 d propyl-amino-c-hydroxybenzoic acid are dissolved in 50 com. of water and to this solution is added a solution of 15 g. of bismuth nitrate in 30 g. of glacial acetic acid. The precipitated new bismuth acid is filtered off, washed with alcohol and dried. It contains 38.8% of bismuth. By dissolving the bismuth acid in a diluted solu tion of sodium carbonate the sodium salt of the bismuth compound is obtained.

The sodium salt which serves as starting material canbe prepared by dissolving g. of 3-amino4-hydroxybenzoic acid in 125 g. of alcohol, adding a solution of sodium ethylate' prepared from 3.5 g. of sodium and 75 com. of alcohol, whereby the sodium salt of this acid is precipitated-and finally condensing the Whole at 40 C. with 11.5 g. of glycide.

(2) To a solution of 32.5 g. of 3-N-dihydroxypropyl-amino 2 hydroxybenzoic acid (obtained by the action of glycide upon 3- amino-salicylic acid) in 100 com. of water is added a solution of g. ofbismuth nitrate in 60 com. of glacial acetic acid and the mixture is allowed to stand for some time. After having neutralized it with a solution of sodium carbonate and added sodium acetate, the bismuth'compound, whose sodium salt is readily soluble in water, reci itates.

(3) 15.3 g. of 3-amino-4-hy oxy nzoic acid are dissolved in the form of its sodium 7 salt in water, then there are added 18 g. of

grape-sugar and the solution is heated on the water bath for three hours. After cooling, there is added a solution of 21.5 g. of hisqnuth nitrate in 45 com; of glacial acetic acid. After some time the whole is neutralized with sodium carbonate and the new bismuth con'ipound is then precipitated by means of sodium acetate.

(4) A mixture of 19.6 g. of gluconic acid, 15.3 g. of 3-amino-2-hydroxybcnzoic acid and 150 g. of Water is heated for 3 hours. After cooling, 19.6 g. of bismuth nitrate, dissolved in 40 com. of glacial acetic acid, are added and the Whole is made up as indicated in Example 3.

(5) 15.3 g. of 3-amino-d-hydroxybenzoic acid are dissolved in glacial aceticacid and mixed with a solution of 21.5 g. of bismuth nitrate in com. of glacial acetic acid. Atter having added a solution of sodium acetate, the resulting bismuth compound is lilterecl off and heated in the form of its sodium-salt-in aqueous solution with grapesugar. The compound thus obtained is identical with that produced according to Example 8.

Theprobable constitution of the product formed in accordance with Examplel is indicated by the following formula:

E trample 1 COONa COOH -NH-o11,-cHon -cmon The probable constitutionof the acid obtained according to Example 3 is indicated by the tormula:

n rwnonncmon Bi(OH)z I The probable constitution of the acid obtained according to Example 4 is indicated causing salts of the trivalent bismuth and 15 by the formula: compounds which are capable of causing the C003 linking of a lateral aliphatic hydrbxyl-com taininggroup to the amino group to act in any order of succession upon amino-phenols. K M 2. As-new products, the bismuth com- 20 pounds of the o-amino-phenols having CO(CHOH).CH'OH aliphatic lateral chains containing hydroxyl Having now described our invention what w h are linked to the yl y all 31111110 10 'we claim is: group.

1. The processfor preparing aromatic bis- In testimony whereof, we affix our signa- 25 muth compounds having aliphatic lateral I chains containing hydroxyl which are linked M BOCKMUHL- 1 to the aryl by an amino group, consisting in Dr. WILHELM mzmmcu LUDWIG. 

